Physical Sciences and Mathematics Commons^™

A Simpler Route To Building Photochromic Cinnamaldehyde Semicarbazones, Byron R. Ebbert

Masters Theses

Photochromic semicarbazones are an interesting group of compounds that show potential in a broad range of applications, including as a more environmentally friendly replacement for photochromic metal complex compounds. Previous work has shown the feasibility to synthesize photochromic cinnamaldehyde semicarbazones (CSCs) from a benzaldehyde and a protected acetaldehyde Wittig reagent. A new, quicker, and cheaper approach to constructing these CSCs from crotonaldehyde was explored in this research. A three reaction sequence would convert crotonaldehyde to a CSC; first, an allylic bromination of the semicarbazone with N-bromosuccinimide (NBS); second, an Arbuzov reaction to prepare the semicarbazone phosphonate; and finally a condensation …